Vitamin C prodrugs and uses thereof

• US 9,550,744 B2
• Filed: 09/24/2014
• Issued: 01/24/2017
• Est. Priority Date: 09/25/2013
• Status: Active Grant

• Current Assignee: University of Florida Research Foundation, Incorporated (State University System of Florida)
• Original Assignee: University of Florida Research Foundation, Incorporated (State University System of Florida)
• Inventors: Sloan, Kenneth B.
• Primary Examiner(s): Katakam, Sudhakar
• Application Number:
  US15/024,504
• Publication Number:
  US 20160264541A1
• Time in Patent Office: 853 Days
• US Class Current: 1/1
• CPC Class Codes: A61P 17/00 Drugs for dermatological disorders
• CPC Class Codes: A61P 3/02 Nutrients, e.g. vitamins, minerals
• CPC Class Codes: C07D 307/62 Three oxygen atoms, e.g. ascorbic acid
• CPC Class Codes: C07D 405/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 405/14 containing three or more hetero rings
• CPC Class Codes: C07D 407/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 407/14 containing three or more hetero rings

Abstract

Described herein are vitamin C prodrugs of Formula (I), (II), or (III), and pharmaceutically acceptable salts thereof. Also provided are pharmaceutical compositions, cosmetic or personal care composition, neutraceutical composition, and medical food composition thereof. Methods of using the compounds or compositions thereof for treating diseases are also provided.

Claims

1. A compound of Formula (I):

2. The compound of claim 1, wherein the compound is of Formula (II):

3. The compound of claim 2, wherein the compound is of Formula (III-a):

4. The compound of claim 2, wherein the compound is of Formula (III-a1-ii):

5. The compound of claim 2, wherein the compound is of Formula (III-a2):

6. The compound of claim 2, wherein the compound is of Formula (III-a2-i):

7. The compound of claim 1, wherein R₆₁ and R₆₂ are each independently optionally substituted C_1-6 alkyl;

or a pharmaceutically or cosmetically acceptable salt thereof.

8. The compound of claim 1, wherein the compound is of Formula (III-b):

9. The compound of claim 1, wherein the compound is of Formula (III-b1) or (III-b2):

10. The compound of claim 1, wherein R₅₁ and R₅₂ are independently hydrogen or optionally substituted C_1-6 alkyl;

or a pharmaceutically or cosmetically acceptable salt thereof.

11. A pharmaceutical composition comprising a compound of claim 1, or a pharmaceutically acceptable salt thereof;

and a pharmaceutically acceptable excipient.

12. A cosmetic or personal care composition comprising a compound of claim 1, or a cosmetically acceptable salt thereof;

and a cosmetically acceptable excipient.

13. A nutraceutical composition comprising a compound of claim 1 and optionally a nutraceutically acceptable carrier.

14. A medical food composition comprising a compound of claim 1 and optionally a nutritionally acceptable carrier.

15. A method of preparing a compound of claim 1 comprising reacting a compound of Formula (i):

16. A method of preparing a compound of claim 1 comprising alkylating a compound of formula (i):

17. A method of making a compound of claim 1, the method comprising steps of:

acylating a compound of Formula (i);

18. A method of making a compound of claim 1, the method comprising steps of:

alkylating a compound of Formula (i);

19. The compound of claim 1, wherein the compound is of Formula (III):

20. The compound of claim 1, wherein the compound is of Formula (III-a1):

21. The compound of claim 1, wherein the compound is of Formula (III-a1-i):

22. The compound of claim 1, wherein R₆₁ and R₆₂ are each independently —

O(CH₂CH₂O)_sCH₃, wherein s is 1, 2, 3, or 4.

23. The compound of claim 1, wherein the compound is of Formula (E-1):

24. The compound of claim 1, wherein the compound is of Formula (E-2):

25. The cosmetic or personal care composition of claim 12, wherein the composition is suitable for topical administration.